{(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol

Base Information

• Chemical Name: {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol
• CAS No.: 328535-14-4
• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.493

Synonyms:{(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol

Chemical Property of {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol

There total 18 articles about {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

tert-Butyl-{(2S,6R,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethoxy}-diphenyl-silane (247184-51-6) → {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol (328535-14-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo001433n

Reference yield:

(2S)-6-benzyloxy-1-(tert-butyldiphenylsilyloxy)-hex-4-yn-2-ol (243464-44-0) → {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol (328535-14-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 78 percent / H₂ / Pd/C / ethyl acetate / 6 h / 760.05 Torr

2.1: 75 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 22 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

3.2: 87 percent / tetrahydrofuran; hexane / 0.83 h / -78 °C

4.1: 97 percent / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 0.58 h / 0 °C

5.1: CuI / tetrahydrofuran; diethyl ether / -78 - -40 °C

5.2: 99 percent / tetrahydrofuran; diethyl ether / 0.42 h / -78 °C

6.1: 76 percent / TsOH*H₂O / benzene / 2.5 h / 20 °C

7.1: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With dmap; copper(l) iodide; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/jo001433n

Reference yield:

(2S,10S,11R)-1-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-12-(4-methoxy-benzyloxy)-11-methyl-10-trimethylsilanyloxy-dodec-7-yn-6-one (328534-76-5) → {(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol (328535-14-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / Et₃N; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 0.58 h / 0 °C

2.1: CuI / tetrahydrofuran; diethyl ether / -78 - -40 °C

2.2: 99 percent / tetrahydrofuran; diethyl ether / 0.42 h / -78 °C

3.1: 76 percent / TsOH*H₂O / benzene / 2.5 h / 20 °C

4.1: 84 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With dmap; copper(l) iodide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo001433n

upstream raw materials:

tert-Butyl-{(2S,6R,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethoxy}-diphenyl-silane

p-Anisaldehyde dimethyl acetal

(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxyhexanoic acid δ-lactone

{(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane

Downstream raw materials:

(2S,5R)-2-tert-Butyl-5-{(2S,6S,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-5-methyl-[1,3]dioxolan-4-one

(2S,5S)-2-tert-Butyl-5-(hydroxy-{(2S,6R,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methyl)-5-methyl-[1,3]dioxolan-4-one

(2S,5R)-2-tert-Butyl-5-(hydroxy-{(2S,6R,8S)-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methyl)-5-methyl-[1,3]dioxolan-4-one

(2S,6R,8S)-8-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde

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